Producing alkyl-isopropylene-phenols



Fatented 2 8,

UNITED STATES PATENT e l-"Pica HANS JORDAN, OF IBERLIN-STEGLITZ,GERMANY, ASSIGNOR T SCHERING-KAHLBAUM AKTIENGESELLSCHAFT, OF BERLIN,GERMANY PRODUCING ALKYL-ISOPROPYLENE-PHENOLS.

11o Drawing. Application filed August My invention refers to thepreparation of chemical products vand more especially to productsobtained b effecting decomposition of the products 0' condensationobtained from alkyl phenols and ketones. Theseprodducts of condensationand the way of producing same were described in mycopending applicationfor patent of the United States Serial No. 200,289, and a method ofeffecting 0 their decomposition by heating them to about are required,such as Al,

of decomposition so instead of the condensation products, which woulddistil over in the absence ofa catalyst, their products of decompositionwill distil 300 0., is disclosed in another copending application SerialNo. 200,290.

I have now found that I can decompose these condensation products atconsiderably a y 15 lower temperatures and obtain a greater yield ofunsaturated phenols, if the heat treatment is carried through in thepresence of a suitable catalyst. Only small quantities, per cent andeven less,

Mg or Hg, or of compounds of such metals, for instance oxids,

or better still their phenolates or the respecover.

Example 1 v To the product obtained by condensing m-cresol and acetonewith gaseous hydrochloric acid at a temperature slightly exceeding roomtemperature, expelling the cresol 0 in excess with steam and distillingthe residue in vacuo, as described in my copending application SerialNo. 200,289 is added a solution of 0.1 per cent by weight of aluminum-3-methyl-G-isopropylene phenolate and the mix ture is heated to about 180distillation results in the formation of dimethyl cumaran is admixed.

The phenolate mentioned above can be replaced for instance by thecorresponding say 0.1 of a suitable metal C in vacuo. The

3- methyl-6-isopr0pylene phenol to which some magnesium compound or byaluminium phenolate, the result being the same in both cases.

Various 'chan'ges may be made in thedetails disclosed in the foregoingspecification without departing from the invention or sacrificing theadvantages thereof.

The term metal in the claims is intended to include also any compound ofsuch metal.

I claim r 1. The process of producing methylisopropylenephenols'comprising heating a compound of the formula 7 a on3' 1. on om'a, e

' ora om in the presence of a metal of the second and third group of theperiodic system.

2. The process of producing methylisopropylene phenols comprisingheating a compound of the formula in the presence of a compound of ametal of the second and third groupof'the periodic iystem which iscapable of forming a phenoate. v, I

3. The process 'of producing mcthylisopropylene phenols comprisingheating a com-- pound of the formula OH oH om 5 on/ om I OH:

in the presence of a metal phenolate of the a, 1927, Serial no. 211,637,n in Germany Au ust n 192 second and third tem.

4. The process of producing 3-methyl-6- isopropylene phenol comprisingheating a compound of the formula group of the periodic sysc 0113 om toa temperature of about 180 C. in the presence of about 0.1% aluminiumphenolate.

5 The; process of producing 3-methyl-6- isopropylene phenol comprisingheating a compound of the formula CHI in vacuo to a temperature of about180 C. in the presence of about 0.1% phenolate of a metal of the secondand third group of the periodic system.

6. The process of producing 3-metl1yl-6- isopropylene phenol comprisingheating the compound having the formula 1 on, I on,

on/ oH,

in vacuo to a tem erature. of about 180 C. in the presence 0 about 0.1%aluminum-3- methyl-6-isopropylene phenolate.

In testimony whereof I aflix my signature.

HANS JORDAN.

